3-arylpropionic Acids Research Articles

Direct Oxidative Cyclization of 3-Arylpropionic Acids to 3,4-Dihydrocoumarins: Reinvestigation of the Reaction Mechanism.

Instigated by olfactory analysis of odorant molecules, the constitutions of 3,4-dihydrocoumarins prepared by PIFA-based oxidative cyclizations of 3-arylpropionic acids were revised by means of 2D NMR and X-ray analysis. Supported by computational analysis, the migratory mechanism of intermediate spirolactonic cations has been amended: 1,2-alkyl shifts instead of 1,2-carboxylic shifts were selectively obtained.

Visible-Light-Driven Anti-Markovnikov Hydrocarboxylation of Acrylates and Styrenes with CO 2

Light-driven carbon dioxide (CO2) capture and utilization is one of the most fundamental reactions in Nature. Herein, we report the first visible-light-driven photocatalyst-free hydrocarboxylation ...

One-pot Synthesis of Dibenzyls and 3-Arylpropionic Acids Catalyzed by Linear Polystyrene-Stabilized Palladium Oxide Nanoparticles in Water

Wat-er transformation! Linear, polystyrene-stabilized PdO nanoparticles (PS-PDONPs) are active catalysts for one-pot, multistep reactions in water. The one-pot synthesis of dibenzyls by sequential Suzuki coupling of β-bromostyrene with arylboronic acid and subsequent hydrogenation was achieved. The catalyst was recycled without significant loss of activity. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Rhodium(I)-Catalyzed 1,4-Addition of Arylboronic Acids to Acrylic Acid in Water: One-Step Preparation of 3-Arylpropionic Acids

A practical method for the one-step preparation of 3-arylpropionic acids through rhodium-catalyzed 1,4-addition of arylboronic acids to acrylic acid is reported. The method is applicable to a broad scope of aryl boronic acids and displays a wide functional group tolerance operating in water as the optimal reaction medium.

Direct oxidative cyclization of 3-arylpropionic acids using PIFA or Oxone: synthesis of 3,4-dihydrocoumarins

The direct oxidative cyclization of 3-arylpropionic acids using PIFA or Oxone is reported. In the presence of BF 3·OEt 2, the reaction of 3-arylpropionic acids with PIFA or Oxone proceeded smoothly at 30 °C to give 3,4-dihydrocoumarins in good to excellent yields.

Synthesis of 3-Arylpropenal and 3-Arylpropionic Acids by Palladium Catalysed Heck Coupling Reactions: Scopes and Limitations

Several classical methods were described for the selective synthesis of cinnamaldehyde derivatives and 3-arylpropionic acids but their applicability remains limited due to the difficult and costly synthesis of the starting materials. Since few years, palladium cata- lyzed procedure has been reported. Whatever they use homogeneous or heterogeneous palladium catalysts, these catalytic methods offer viable environmental friendly alternatives to stoechiometric methods particularly since they generally required a single reaction step start- ing from simple substrates. Some of these new methods are really considered as green alternatives since they use heterogeneous easily separable (and recyclable) palladium catalysts. This review article summarizes the literature on this area. It is ended by mechanistic considerations.

SAR studies of 3-arylpropionic acids as potent and selective agonists of sphingosine-1-phosphate receptor-1 (S1P 1) with enhanced pharmacokinetic properties

Structure–activity relationship (SAR) studies of 3-arylpropionic acids—a class of novel S1P 1 selective agonists—by introducing substitution to the propionic acid chain and replacing the adjacent phenyl ring with pyridine led to a series of modified 3-arylpropionic acids with enhanced half-life in rat. These analogs (e.g., cyclopropanecarboxylic acids) exhibited longer half-life in rat than did unmodified 3-arylpropionic acids. This result suggests that metabolic oxidation at the propionic acid chain, particularly at the C3 benzylic position of 3-arylpropionic acids, is probably responsible for their short half-life in rodent.

Discovery of 3-arylpropionic acids as potent agonists of sphingosine-1-phosphate receptor-1 (S1P 1) with high selectivity against all other known S1P receptor subtypes

A series of 3-arylpropionic acids were synthesized as S1P 1 receptor agonists. Structure–activity relationship studies on the pendant phenyl ring revealed several structural features offering selectivity of S1P 1 binding against S1P 2–5. These highly selective S1P 1 agonists induced peripheral blood lymphocyte lowering in mice and one of them was found to be efficacious in a rat skin transplantation model, supporting that S1P 1 agonism is primarily responsible for the immunosuppressive efficacy observed in preclinical animal models.

Direct synthesis of 3-arylpropionic acids by tetraphosphine/palladium catalysed Heck reactions of aryl halides with acrolein ethylene acetal

Through the use of [PdCl(C 3H 5)] 2/ Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides undergoes Heck reaction with acrolein ethylene acetal. With this acetal, the selective formation of 3-arylpropionic acids/esters was observed. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.

Synthesis of 1‐Indanones by Intramolecular Friedel—Crafts Reaction of 3‐Arylpropionic Acids Catalyzed by Tb(OTf)3.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis of 1-indanones by intramolecular Friedel–Crafts reaction of 3-arylpropionic acids catalyzed by Tb(OTf) 3

Intramolecular Friedel–Crafts acylation reaction of 3-arylpropionic acids was efficiently catalyzed by Tb(OTf) 3 at 250 °C to give 1-indanones. Even deactivated 3-arylpropionic acids with halogen atoms on the aromatic ring can be cyclized in moderation to good yields.

Pseudoguaianolides from intramolecular cycloadditions of aryl diazoketones: synthesis of (±)-confertin and an approach to the synthesis of (±)-damsin

Rhodium (II) mandelate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acids produces bicyclo[5.3.0]decatrienones, one of which has been used to synthesise an advanced (±)confertin intermediate in six stages and 20% overall yield. The possibility of constructing intermediates for the synthesis of damsin-like pseudoguaianolides via catalysed diazoketone cyclisation is also examined and methods for the construction of polyfunctional 3-arylpropionic acids suitable for use as damsin precursors are presented.

Efficient synthesis of bicyclo[5.3.0]decatrienones and of 2-tetralones via rhodium(II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acids

Rhodium (II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acid produces bicyclo[5.3.0]decatrienones or 2-tetralones depending on the substitution pattern of the aryl ring: the former products are transformed into the latter by catalytic amount of trifluoroacetic acid.

The synthesis of arylpropionic acids and the quantitative relationship between the structure and the activation of fibrinolysis

A number of substituted 2-arylpropionic (IV) and 3-arylpropionic (V) acids were prepared and their activity in the activation of fibrinolysis and the inhibition of heat denaturation of serum albumin was evaluated. The results were worked up using the method of regression analysis. From the regression equations obtained it may be considered that both activities are affected mainly by the lipophilicity of the aromatic substituents. The effect of the branching in the connecting chain between the carboxyl group and the aromatic ring is negligible in both activities. The linear dependence of the fibrinolytic capacity on lipophilicity is in both series of acids, IV and V, characterized by a distinct decrease in activity, following the attainment of the optimum value of lipophilicity. In the series of cinnamic acids (VI) regression equations concerning the inhibition of the denaturation of serum albumin and the activation of fibrinolysis were also calculated, showing a linear dependence of these activities on the lipophilicity of the varying substituents R and X. Summary regression equations were derived for both activities in the whole set of acids I-VI. Both the inhibition of the denaturation of serum albumin, and the activation of fibrinolysis depends on the lipophilicity of the mentioned acids exclusively. The modification of the connecting chain between the carboxyl group and the aromatic ring affects both activities primarily by the corresponding change in lipophilicity.

A new enzyme model system showing marked substrate specificity

The water-soluble steroid (I) acts as a catalyst for the hydrolysis of active esters, with a definite specificity for esters of 3-arylpropionic acids, the ester of 3-(3-phenanthryl)propionic acid being the most rapidly hydrolysed substrate found to date; it is concluded that imidazole-catalysed hydrolysis of the esters is facilitated by hydrophobic interactions between substrate and catalyst.